There is essentially no reason to bother with PHP these days. It's a relic and you'd end up having to learn all sorts of arbitrary distracting things.

I can empathise with the intimidation. There was a whole heap of linux administration stuff that I had to pick up to get started. Fortunately, you don't need to do anything like that any more and it can be even easier on windows! You can install the whole stack (ie. Ruby, Rails, apache and mysql) all at once. From there you can just find a tutorial to follow then start copy and pasting stuff from similar applications till you have one that does what you want. (You didn't hear 'develop by cut and paste and google' from me! ;))

RubyStack is one option. The one I have used is InstantRails. I think that one is getting out of date (about a year old) but it probably doesn't make any difference for your purposes.

I don't know what the options are for other web development frameworks. I'm sure there is something simple out there for Python somewhere but I just haven't had reason to look into it.

So if you wanted to get started it is easy enough. Depends on your interest.

How do most people get started with this whole hacker thing?

When I have something I want to do I go do it. Sometimes that means learning stuff like programming. Sometimes it means learning pharmacology. That's probably the underlying spirit behind the 'hacker' mindset.